Nicotine glucuronide (CHEM022510)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:37:58 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022510
Identification
Common NameNicotine glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltChEBI
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylateChEBI
Nicotine N-glucuronideChEBI
(S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltGenerator
(S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltGenerator
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acidGenerator
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner saltHMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner saltHMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltHMDB
1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridiniumHMDB
1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridiniumHMDB
1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridiniumHMDB
1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridiniumHMDB
Nicotine-glucuronideHMDB
Chemical FormulaC16H22N2O6
Average Molecular Mass338.356 g/mol
Monoisotopic Mass338.148 g/mol
CAS Registry Number152306-59-7
IUPAC Name1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium
Traditional Namenicotine glucuronide
SMILESCN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O
InChI IdentifierInChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1
InChI KeySAWAIULJDYFLPD-SOAFEQHCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Hydroxypyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.02 g/LALOGPS
logP-1.6ALOGPS
logP-7.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)7.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.17 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.18 m³·mol⁻¹ChemAxon
Polarizability33.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9363000000-498032dac1d25a048f1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000l-6695530000-5f3cb4632382491d1884Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-c0a6517967854466764fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-3209000000-9c96a94c455824fbcb27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-6911000000-358133c8eb23ea49be3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-470460c450e2ce5dc00fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-5594000000-c8f1d538ca13bdab946dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-83503a4041514150d674Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0209000000-45aaad3735689e97aa1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yr-0905000000-ca062e765a6a892950c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-3910000000-d6d53f13a1744fd96f8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0229000000-8425edbf57e8743a529bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-5977000000-71e200566908d48e305dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-8941000000-0a955908878509d2a872Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001272
FooDB IDFDB022526
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6127
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2299987
ChEBI ID63860
PubChem Compound ID3035848
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Heavner DL, Richardson JD, Morgan WT, Ogden MW: Validation and application of a method for the determination of nicotine and five major metabolites in smokers' urine by solid-phase extraction and liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2005 May;19(4):312-28.
2. Tulunay OE, Hecht SS, Carmella SG, Zhang Y, Lemmonds C, Murphy S, Hatsukami DK: Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer Epidemiol Biomarkers Prev. 2005 May;14(5):1283-6.
3. Hecht SS, Carmella SG, Chen M, Dor Koch JF, Miller AT, Murphy SE, Jensen JA, Zimmerman CL, Hatsukami DK: Quantitation of urinary metabolites of a tobacco-specific lung carcinogen after smoking cessation. Cancer Res. 1999 Feb 1;59(3):590-6.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11201307
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11846386
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15265511
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21497036
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7902257